To tuck or not to tuck? That is the question.
Depends on the shirt (cue everyone sarcastically saying "thanks for that answer"). OK, for button down shirts, and I would say specifically OCBDs there are shirts designed to be untucked:
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And ones designed to be tucked:
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The ones designed to be untucked will be shorter and more fitted at the bottom (personally I like it when the "bib" at the bottom sort of separates). The "tucked" ones are longer and probably a little less fitted (think a suit dress shirt). The longer length keeps them tucked in, just as trying to keep a shirt designed to be untucked tucked in always leads to them coming out.
As for polo shirts, I always think whomever is wearing them tucked in is sneaking off to play a round of golf, like in Curb Your Enthusiasm.
I thought it was interesting JT on the VMA's had an untucked shirt with a jacket.
The pictures above: to me the shirts are too long and look silly un-tucked. Especially the top. Tuck that shirt in with a cool belt unitil you get a better fit The second is more fitted but the shirt should come down to the top or mid crotch, any longer and the shirt looks silly. It should be tight to your abs no flapping wavy fabric. I think the straight cut bottom looks better than the scalloped cut. T shirts untucked and short and tight on the arm not a flapping sleeve. Every Jerbroney that goes out with their jeans, dress shoes and untucked long un fitted shirts looks silly and so common, I just hate the look. A nice fitting short shirt untucked works better. It is more about the fit and look as a whole than one element of in or out. You can rock it either way or look like your are trying to hard (which is most common because people don't pay attention to the real details). "Oh untucked is in style", no the type of shirt matters, tighter in the arms and cut to the arm pits, slimmed down by the abs and shorter.
I mostly wear guayaberas, certainly not an ocbd that can or should be tucked in...
T-shirt untucked. Polo goes either. Dress shirt always
Thirded.This.